Tetrahydrofuran → {(S)-4-[4-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-pyrazol-1-yl]-pyrrolidin-2-yl}-methanol

HRID 1926362Notes

Reaction equation

HRID 1926362 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][N:11]([C@@H:13]3[CH2:17][NH:16][C@H:15]([C:18](O)=[O:19])[CH2:14]3)[CH:12]=2)=[CH:4][C:3]=1[C:21]1[S:22][C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=1.C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][N:11]([CH:13]3[CH2:17][NH:16][C@H:15]([CH2:18][OH:19])[CH2:14]3)[CH:12]=2)=[CH:4][C:3]=1[C:21]1[S:22][C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 44160252(2S,4S)-4-[4-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-pyrazol-1-yl]-pyrrolidine-2-carboxylic acid

Product 1

HCID 67521863{(S)-4-[4-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-pyrazol-1-yl]-pyrrolidin-2-yl}-methanol

Procedure

A solution of (2S,4S)-4-[4-(6-amino-5-benzothiazol-2-ylpyridin-3-yl)-pyrazol-1-yl]-pyrrolidine-2-carboxylic acid (10.0 mg, 0.0155 mmol) in THF (4 mL, 0.05 mol) was cooled to −78° C. LiAlH4 (1.0 M in THF; 0.2 mL, 0.2 mmol) was added slowly, and the mixture was allowed to warm to rt overnight. The material was concentrated in vacuo, then dissolved in DCM, transferred to a separatory funnel, and washed with sat. NaHCO3. The organic layer was loaded onto a prep TLC plate, eluting with 8% (7N NH3 in MeOH)/DCM. The band containing the product was filtered off using 1:1 MeOH/DCM. The filtrate was concentrated in vacuo to afford the title compound (mixture of diastereomers) as a yellow solid. MS (ES+): m/z=393.14 [MH+].

Workup

  1. concentrationThe material was concentrated in vacuo
  2. dissolutiondissolved in DCM
  3. customtransferred to a separatory funnel
  4. washwashed with sat. NaHCO3
  5. washeluting with 8% (7N NH3 in MeOH)/DCM
  6. additionThe band containing the product
  7. filtrationwas filtered off
  8. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f37ea8aacbfa480282b88ea961c4d9a4
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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